Risky Tips [With Kate Quigley]: Reeling in a New Relationship Without Scaring Them Off


In this week’s Risky Tips, comedian Kate Quigley addresses the age-old wives tales of monogamy and what to do when you’re on the brink of exclusivity in a new relationship. How do you reel them in? Kate has a few suggestions, some riskier than others. When you’re done here, be sure to check out the latest episode of her podcast, #DateFails.

Hey Kate!

I have a question that I’d love to hear your perspective on since dating in our 30s is so awkward. If you’ve been going on dates with a guy you really like and finally hook up after the fourth or fifth date, when do you decide to become exclusive? And how do you bring this up in a way that doesn’t make him want to run? (We have plans to see each other twice this week so it wasn’t a one-night stand.) Would love your thoughts.

Love the podcast!

Clueless & Crushing Hard

Hi C&CH!

Oh boy, you have asked the most mysterious question in the history of dating! It should be simple. Man likes woman. Woman likes man. Man courts woman. Man gets to have consensual sex with woman. Suddenly, they’re dating exclusively without having any real conversation about it.

Unfortunately, we live in times where people are terrified to commit and have the attention span of a toddler. Dating apps and social media have made the options seem endless, and everyone’s relationship appears to be perfect in comparison to ours, which makes exclusivity extra scary.

There are a few ways you could go about it, but I’m going to give you all the ones I have used successfully (granted, I’m currently extremely single so keeping him around is clearly another story). 

Most experts will tell you this conversation should happen before the sex, but since it’s a little late for that, I’ll give you my two cents on what has worked for me…

Try Something Unique to Dating: Honesty

I know, it’s risky and makes you extremely vulnerable, but if it’s really what you want, be direct.

Tell him that you don’t have sex casually and that if he wants to continue to sleep with you, he’s going to have to avoid sleeping with the strays. Steve Harvey says to make him wait for ninety days, but we haven’t got that kind of time! If there’s a true connection, I’m typically dying to get naked by date two. I can fight it until date four if I don’t shave, feel fat, or get lucky and get my period.

My best guy friend gave me the most real guy advice ever, and he has told me to say this:

“I am really feeling like this is more than casual. I’d like to keep dating you, but at this point, I wouldn’t really be comfortable with you seeing other people. It doesn’t mean I want to move in or for anything else to change, but how would you feel about being exclusive?”

Now here’s the important part. My male friends all agree that once you say this, if he says no for any reason, you must be willing to walk away. And you must stick to it. If you do it and let the guy miss you, he will either come back or realize he didn’t feel enough for you to commit. Either way, you’ll know.

Simply, Pull Out

This one is a little bit of game playing, which I hate doing, but it has worked many times: Be less available.

Turn down a date or two with vague “dinner plans.” Or just simply forget to answer a text here and there. Just like that, he’ll be curious about what’s happening. Oh, and on that note, do see someone else. It’s hard to do when we like someone, but don’t you dare start giving him all of your time and attention until you know he wants it and is doing the same. This goes for guys as well.

I have invested too much too soon many times. It’s always a recipe for heartbreak if you find out the other side was never as smitten as you. Keep your options open until he asks you not to. Four or five dates is quick. Make sure they’re worthy of your commitment! I understand though, sometimes you just feel it all so fast and get excited. Life is short. Follow your heart if your head agrees.

risky tips


Put the Balls in His Court

This one may raise some eyebrows, but this has been my most effective strategy. Tell him you don’t want to use condoms.

I know, it’s conniving (and risky, but that’s the name of the game here). But the truth is if you’re both exclusive, tested and using birth control, this is how it would end up eventually anyway. Everybody hates condoms so this has easily worked for me in the past. Just expedite the process, if you think he can be trusted. If he asks why, tell him you like having spontaneous sex in random places. Guys eat it up (sorry guys).

The downside of this, because it’s based on something so physical, I’d be concerned that he may lie to have sex without condoms. It wouldn’t be the first time in this not-so-brave new dating app world. So make sure the person is trustworthy before you go there. And definitely make sure they’re clean beforehand. Just be careful (of your heart and private parts).

Go for Broke: Keep a Closed Circle

This is the Hail Mary. It’s highly unconventional, but if it’s true for you, it couldn’t hurt to try it. Tell him you’re interested in some seriously kinky stuff down the road, but for committed boyfriends only. I’m aware this is a bit conniving, and could be considered reeling him in with the wrong selling points, but there’s occasionally a go-for-broke moment we have with people we feel a strong connection to that we want to maintain.

Definitely don’t go there, if it’s not something you’re into, but if it is, there’s no harm in talking about sex. Especially if it’s something that’s important to both of you. Just make sure you’re willing to back it up, so to speak.

All this to say, these suggestions are mostly in order of operation. Try to be honest first, then maybe pull back if you feel that honesty would scare him off. Before you even consider manipulating his desires to have unprotected and kinky sex, make sure this is someone you trust completely. This early on in a relationship that can be tough to do, so weigh it heavily before using this option!

Make sure he’s worth it before you engage these last ideas. Dating isn’t always fun, but new relationships and sex with someone you trust are! Remember that the next time you’re with him and see if he measures up. Communication is key. If you can’t communicate, all you have is hot sex with a guy you can’t talk to, which is fun at times, but definitely not what you want from this one!

Hope this helped! Keep me posted!

Love you!

Kate xoxo

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Then be sure to tune in for the latest #DateFails below.



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